Located in the heart of Sea Pines on Hilton Head Island, The Hamilton is a beautifully furnished 5-bedroom, 5.5-bath legacy home available for extended monthly stays from November through April.
With over 5,400 square feet of refined living space, this thoughtfully designed home comfortably accommodates up to 10 guests—perfect for families or couples looking to settle into coastal life for a season.
Just seven rows from the Atlantic Ocean, this beach-oriented home invites you to relax, recharge, and enjoy Hilton Head at your own pace. The Beach Walk is conveniently located behind the street, and the bike path out front makes exploring a breeze. Ride just a mile to the iconic Salty Dog Café or head three miles to the charming shops and waterfront of Harbour Town. The Hamilton's setting is truly special—nestled along a peaceful lagoon with private views and beautifully manicured grounds.
Step inside and discover warm, coastal-inspired interiors, multiple gathering spaces, and quiet nooks to unwind. The spacious kitchen and dining areas are perfect for entertaining, while multiple decks and patios allow you to soak in the Lowcountry air. Enjoy a game of pool, grill out on the deck, or take a dip in the heated pool (available by request for an additional fee). With amenities like air conditioning, laundry, and ample room to spread out, every detail has been considered for your comfort.
Included With Your Stay: • Private Pool (Heat Optional for an Additional Fee) • Game Room w/ billiard table • Access to the Sea Pines Trolley • Access to Sea Pines Beach Club Beach Access (Labor Day - Memorial Day) • Starter amenities and keyless entry • Sea Pines Community Guidelines
Sleeping Arrangements: Bedroom 1: 1x King Bed Bedroom 2: 2x Twin Beds Bedroom 3: 1x Queen Beds Bedroom 4: 3x Twin Beds Bedroom 5: 1x Queen Bed
Why Book with Hilton Head Properties R&R? We go beyond the booking to make your stay seamless and memorable. Every reservation includes local perks like complimentary activities through Xplorie (dolphin tour, golf, mini-golf, beach gear & more), dedicated vacation planners to help curate your trip, and a full-time maintenance team ready to assist anytime you need us.
Permit #042884
Our prices include all fees. No hidden fees.
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Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card, or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
Onsite parties or group events are strictly prohibited
Host has indicated there is a carbon monoxide detector on the property
Host has indicated there is a smoke detector on the property
Safety features at this property include a fire extinguisher
This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room
About the neighborhood
Hilton Head Island
Sea Pines, a neighborhood in Hilton Head Island, is home to this vacation home. Shelter Cove Harbour and Palmetto Dunes Club are worth checking out if an activity is on the agenda, while those wishing to experience the area's natural beauty can explore Sea Pines Forest Preserve and Coligny Beach. Gregg Russell Harbour Town Playground and Lawton Stables are also worth visiting.
Beach Club at The Sea Pines Resort - 6 min drive
Frequently asked questions
Is Monthly Rental Dream • 5BR Sea Pines Home on Lagoon | Private Heated Pool, BBQ, Bikes pet-friendly?
No, pets are not allowed at this property.
How much does it cost to stay at Monthly Rental Dream • 5BR Sea Pines Home on Lagoon | Private Heated Pool, BBQ, Bikes?
As of Jun 18, 2026, prices found for a 1-night stay for 2 adults at Monthly Rental Dream • 5BR Sea Pines Home on Lagoon | Private Heated Pool, BBQ, Bikes on Aug 27, 2026 start from $1,179, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.
What time is check-in at Monthly Rental Dream • 5BR Sea Pines Home on Lagoon | Private Heated Pool, BBQ, Bikes?
Check-in begins at 4:00 PM.
What time is check-out at Monthly Rental Dream • 5BR Sea Pines Home on Lagoon | Private Heated Pool, BBQ, Bikes?
Check-out is at 10:00 AM.
Where is Monthly Rental Dream • 5BR Sea Pines Home on Lagoon | Private Heated Pool, BBQ, Bikes located?
Located in Sea Pines, this vacation home is within a 15-minute walk of South Beach and Calibogue Sound. Stoney-Baynard Ruins and Atlantic Dunes by Davis Love III are also within 2 mi (3 km).
Reviews
9.0
Wonderful
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labeled.
We had a awesome time, beautiful home in a peaceful neighborhood..we were so relaxed we extended an extra day!
Shana kay s.
Stayed 5 nights in Sep 2025
Response from VrboOwner on Sep 24, 2025
Thank you so much for your kind words! We’re delighted to hear you had such a relaxing stay and enjoyed the home and neighborhood. We love that you decided to extend your visit—that’s the best compliment we could receive! We’d be happy to welcome you back anytime.
We have been visiting Hilton Head for more than 15 yrs. This is the 4th house we have stayed in. We chose it primarily for the back yard. Unfortunately, a gator kept us from enjoying fishing in the pond as much as we would have liked. The size of the house was great for us. The location was great since we usually stay on this street. The house needs more furntiure. There were 8 of us this trip and the dining room table is the only place we could all gather. That is perfect for dinners but not for relaxing.
REBECCA T.
Stayed 7 nights in Sep 2025
About the host
Hosted by Darcey Sundling, Hilton Head Properties R & R
Hilton Head Properties Realty & Rentals is a vacation rental company that was founded by four long-time islanders who were determined to address the issues of high expenses and poor maintenance prevalent in the industry.
Each founder brought their unique expertise to the table. One had extensive experience in second home maintenance, another had served as a customer service representative for over 1400 individuals, the third was a visionary who brought the team together, and fourth had over 30 years of real estate marketing experience for the properties now in their rental program. Together, they built a team that upholds the founding principles of the company.
The mission statements of Hilton Head Properties R & R reflect our commitment to our clients and guests. We strive to be dependable guardians going above and beyond to create raving fans and make everlasting memories. We value forming partnerships that matter and offering quality places. Above all, the bottom line is that we care.
Hilton Head Properties R & R provides property owners with comprehensive property management, creative rental marketing, concierge guest services, and the most proactive maintenance program available on the island. Our clients and guests can expect exceptional customer service and maintenance at every stage of the rental progress, from before the rental begins to after it ends. Hilton Head Properties R & R aims to exceed expectations and ensure that their guests and owners have a memorable and enjoyable stay.
We hope to provide you with an outstanding experience and look forward to welcoming you as our guest.
Languages:
English
Premier Host
They consistently provide great experiences for their guests